The earliest known reference to a Milwaukee pipe band is from a newspaper article about the 1905 Milwaukee Highland Games, which mentions the "Milwaukee Caledonian Pipe Band".

Little more occurs until some time after World War II, when a band know as the Canadian Legion was organized. This group played until the 1950's, when it evolved into the Milwaukee Highlanders. A fledgling band (the Black Swan) merged with the Highlanders in 1969. Not long thereafter, in 1971, the Pipes and Drums, the Billy Mitchell Scottish, was organized.